WO2008040458A1 - Préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5- méthyl-cyclohexanecarbonyl-d-alanine et une ou plusieurs substances actives d'éclaircissement de la peau conçues pour lutter contre une pigmentation indésirable de la peau, en particulie - Google Patents

Préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5- méthyl-cyclohexanecarbonyl-d-alanine et une ou plusieurs substances actives d'éclaircissement de la peau conçues pour lutter contre une pigmentation indésirable de la peau, en particulie Download PDF

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Publication number
WO2008040458A1
WO2008040458A1 PCT/EP2007/008231 EP2007008231W WO2008040458A1 WO 2008040458 A1 WO2008040458 A1 WO 2008040458A1 EP 2007008231 W EP2007008231 W EP 2007008231W WO 2008040458 A1 WO2008040458 A1 WO 2008040458A1
Authority
WO
WIPO (PCT)
Prior art keywords
skin
isopropyl
cosmetic
preparations
methyl ester
Prior art date
Application number
PCT/EP2007/008231
Other languages
German (de)
English (en)
Inventor
Julia Eckert
Ludger Kolbe
Gitta Neufang
Original Assignee
Beiersdorf Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beiersdorf Ag filed Critical Beiersdorf Ag
Publication of WO2008040458A1 publication Critical patent/WO2008040458A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/223—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of alpha-aminoacids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant

Definitions

  • the present invention relates to cosmetic cosmetic or dermatological preparations containing 2-isopropyl-5-methyl-cyclohexanecarbonyl-D-alanine methyl ester and one or more skin lightening agents against unwanted pigmentation of the skin, in particular postinflammatory hyperpigmentation.
  • melanocytes responsible for the pigmentation of the skin are the melanocytes, which are found in the lowest layer of the epidermis, the stratum basale, in addition to the basal cells - depending on the skin type either isolated or more or less frequently occurring - pigment-forming cells.
  • Melanocytes contain as characteristic cell organelles melanosomes, in which the melanin is formed. Among other things, upon excitation by UV radiation melanin is increasingly formed. This is transported via the living layers of the epidermis (keratinocytes) ultimately in the horny layer (corneocytes) and causes a more or less pronounced brownish to brown-black skin color.
  • DHICA and DHI melanin are produced via the common intermediates dopaquinone and dopachrome. The latter is reacted, sometimes with the participation of other enzymes, either in indole-5,6-quinone carboxylic acid or in indole-5,6-quinone, resulting in the two mentioned Eumelanine arise.
  • Phaeomelanin is produced, inter alia, by the intermediates dopaquinone and cysteinyldopa.
  • the expression of the melanin-synthesizing enzymes is controlled by a specific transcription factor (microphthalmia-associated transcription factor, MITF).
  • MITF microphthalmia-associated transcription factor
  • the size and shape of the melanosomes influence their light-scattering properties and thus the color appearance of the skin.
  • black Africans for example, large spheroidal, isolated melanosomes are increasingly found, whereas in Caucasus, smaller, grouped melanosomes are found.
  • UV radiation e.g., freckles, ephelides
  • genetic predisposition e.g., skin malignancy in wound healing (postinflammatory hyperpigmentation)
  • skin aging e.g., lentigines seniles
  • the present invention relates to cosmetic and dermatological preparations with reduced skin irritation.
  • cooling agents which interact with the heat receptors of the skin and thus trigger a feeling of cold without generating any measurable physical cooling
  • menthol and various menthol derivatives Rescolate, Physcool, Questice L 1, etc.
  • high content of ethane, as well as menthol and its derivatives are not suitable for numerous uses under olfactory aspects in addition to the irritative potential, in particular due to their distinct inherent odor Frequently enough, such substances also increase blood circulation at the same time causes.
  • cooling agents in particular ammonium salts
  • cooling preparations are also widely used isopropanolic gels with camphor and menthol additive.
  • this is for the treatment of the following hyperpigmentation conditions: postinflammatory hyperpigmentation after inflammatory reactions, in particular those associated with shaving, melasma, uneven skin tone, in particular as a result of excessive exposure to the sun.
  • Particularly preferred indications would be postinflammatory hyperpigmentation due to the pseudofollicularis barbae and melasma.
  • 2-Isopropyl-5-methylcyclohexanecarbonyl-D-alanine methyl ester is characterized by the following structure:
  • the organic phase was evaporated under reduced pressure to give 2 g of the final product, which crystallized at room temperature.
  • the expected molecular mass and structure were confirmed by mass spectrometer or NMR spectrum.
  • Particularly advantageous is a use according to the invention, characterized in that the preparations 0.0001 to 5 wt .-%, in particular 0.001 to 1 wt .-%, most preferably 0.005 to 0.15 wt .-% of 2-isopropyl-5-methyl Cyclohexanecarbonyl-D-alanine methyl ester, based on the total weight of the preparation.
  • a use according to the invention is particularly advantageous, characterized in that the preparations contain from 0.001 to 10% by weight, in particular from 0.05 to 5% by weight, very particularly preferably from 0.01 to 2% by weight, of one or more of the skin containing lightening agents, based on the total weight of the preparation.
  • skin lightening agents used in the invention can be selected advantageously:
  • Cosmetic and dermatological preparations according to the invention can be present in various forms. So they can e.g. a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) type or of the oil-in-water (O / W) type, a multiple emulsion, for example of the water-in-oil type in water (W / O / W), a gel, a solid stick, an ointment or even an aerosol. It is also advantageous in the invention to provide folic acid and / or its derivatives in encapsulated form, e.g. in collagen matrices and other common encapsulating materials, e.g. as cellulase encapsulations, in gelatin, wax matrices or liposomally encapsulated. In particular wax matrices as described in DE-OS 43 08 282, have been found to be favorable.
  • the cosmetic and dermatological preparations according to the invention may contain cosmetic adjuvants such as are conventionally used in such preparations
  • cosmetic adjuvants such as are conventionally used in such preparations
  • preservatives bactericides, perfumes, foaming inhibitors, dyes, pigments that have a coloring effect, thickeners, surfactants, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other conventional ingredients
  • a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • the lipid phase can advantageously be selected from the following substance group: mineral oils, mineral waxes
  • Oils such as triglycerides of capric or caprylic acid, further natural oils such as e.g. Castor oil;
  • Fats, waxes and other natural and synthetic fats preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids; benzoates;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions in the context of the present invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms, from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms.
  • ester oils can then advantageously be selected from the group isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2 Octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and also synthetic, semisynthetic and natural mixtures of such esters, eg jojoba oil.
  • the aqueous phase of the preparations according to the invention optionally advantageously contains alcohols, diols or polyols of low C number, and their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or -mob nobutyl ether, propylene glycol monomethyl, -monoethyl- or -monobutylether , Diethylene glycol monomethyl or monoethyl ether and analogous products, furthermore low C-number alcohols, for example ethanol, isopropanol, 1,2-propanediol, glycerol, and in particular one or more thickening agents, which may advantageously be selected from the group silicon dioxide, Aluminum silicates, polysaccharides or their derivatives, for example hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageously from the group of the polyacrylates, preferably
  • mixtures of the abovementioned solvents are used.
  • alcoholic solvents water can be another ingredient.
  • Emulsions of the invention are advantageous and contain e.g. the said fats, oils, waxes and other fatty substances, as well as water and an emulsifier, as commonly used for such a type of formulation.
  • Gels according to the invention usually contain low C number alcohols, e.g. Ethanol, isopropanol, 1, 2-propanediol, glycerol and water or an above-mentioned oil in the presence of a thickener which is preferably silica or an aluminosilicate in oily-alcoholic gels, in aqueous-alcoholic or alcoholic gels, preferably a polyacrylate.
  • a thickener which is preferably silica or an aluminosilicate in oily-alcoholic gels, in aqueous-alcoholic or alcoholic gels, preferably a polyacrylate.
  • Suitable propellants for preparations which can be sprayed from aerosol containers according to the invention are the customary known highly volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be used alone or mixed with one another. Also, compressed air is advantageous to use.
  • compositions according to the invention can also advantageously contain substances which absorb UV radiation in the UVB range, the total amount of the filter substances being, for example, from 0.1% by weight to 30% by weight, preferably from 0.5 to 10% by weight, in particular 1, 0 to 6.0 % By weight, based on the total weight of the preparations, in order to provide cosmetic preparations which protect the hair or the skin from the entire range of ultraviolet radiation. They can also serve as a sunscreen for hair or skin.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne des préparations cosmétiques ou dermatologiques comprenant de l'ester méthylique de la 2-isopropyl-5-méthyl-cyclohexanecarbonyl-D-alanine et une ou plusieurs substances actives d'éclaircissement de la peau.
PCT/EP2007/008231 2006-09-29 2007-09-21 Préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5- méthyl-cyclohexanecarbonyl-d-alanine et une ou plusieurs substances actives d'éclaircissement de la peau conçues pour lutter contre une pigmentation indésirable de la peau, en particulie WO2008040458A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006047157A DE102006047157A1 (de) 2006-09-29 2006-09-29 Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an 2-Isopropyl-5-Methyl-Cyclohexancarbonyl-D-Alaninmethylester und einem oder mehreren hautaufhellenden Wirkstoffen gegen unerwünschte Pigmentierung der Haut, insbesondere postinflammatorische Hyperpigmentierung
DE102006047157.1 2006-09-29

Publications (1)

Publication Number Publication Date
WO2008040458A1 true WO2008040458A1 (fr) 2008-04-10

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Application Number Title Priority Date Filing Date
PCT/EP2007/008231 WO2008040458A1 (fr) 2006-09-29 2007-09-21 Préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5- méthyl-cyclohexanecarbonyl-d-alanine et une ou plusieurs substances actives d'éclaircissement de la peau conçues pour lutter contre une pigmentation indésirable de la peau, en particulie

Country Status (2)

Country Link
DE (1) DE102006047157A1 (fr)
WO (1) WO2008040458A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2205255A1 (fr) * 1971-02-04 1972-11-30
US20060171912A1 (en) * 2005-01-28 2006-08-03 Schwartz James R Diiodomethyl-p-tolylsulfone as a particulate dispersion in a liquid solvent

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0900211B1 (fr) * 1996-04-23 2003-07-02 PHARMACIA & UPJOHN COMPANY Thiadiazolyl(thio)urees utiles comme inhibiteurs de metalloproteases a matrice
GB9918030D0 (en) * 1999-07-30 1999-09-29 Unilever Plc Skin care composition
US20050048012A1 (en) * 2003-08-26 2005-03-03 Roland Jermann Use of biotin or a biotin derivative for skin lightening purposes and for the treatment of senile lentigines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2205255A1 (fr) * 1971-02-04 1972-11-30
US20060171912A1 (en) * 2005-01-28 2006-08-03 Schwartz James R Diiodomethyl-p-tolylsulfone as a particulate dispersion in a liquid solvent

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WATSON H R ET AL: "NEW COMPOUNDS WITH THE MENTHOL COOLING EFFECT", JOURNAL OF THE SOCIETY COSMETIC CHEMISTS, SOCIETY OF COSMETIC CHEMISTS,, US, vol. 29, no. 4, 1978, pages 185 - 200, XP009045124, ISSN: 0037-9832 *

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